Iodoethane → 2-(2-Iodophenyl)butanoic acid

HRID 342005Notes

Reaction equation

HRID 342005 reaction equation
[CH:1](NC(C)C)(C)[CH3:2].[Li]CCCC.[I:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([OH:23])=[O:22].ICC>C1COCC1>[I:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([CH2:1][CH3:2])[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 7912DiisopropylamineHCID 27800902-Iodophenylacetic acidHCID 178418339Butyllithium

Product 1

HCID 224564332-(2-Iodophenyl)butanoic acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diisopropylamine (5.6 mL, 40 mmol) in dry THF (60 mL) at -10° C. was added 1.6M BuLi (25 mL, 40 mmol). After 30 min, a solution of 2-iodophenylacetic acid (5.24 g, 20 mmol) in THF (20 mL) was slowly added. The solution was stirred for 1 h, at which point iodoethane (1.6 mL, 117 mmol) was added. After 2 h at r.t. the reaction was quenched with 0.5M NH4OAc solution and 6M HCl (10 mL) and the product was extracted with EtOAc. The organic layer was dried (MgSO4) and evaporated to give an oily residue which was purified by flash chromatography (15:85 EtOAc:hexane containing 5% AcOH) to give 4.37 g of the title compound as an off-white solid.

Workup

  1. additionwas added
  2. customAfter 2 h at r.t. the reaction was quenched with 0.5M NH4OAc solution and 6M HCl (10 mL)
  3. extractionthe product was extracted with EtOAc
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customto give an oily residue which
  7. customwas purified by flash chromatography (15:85 EtOAc:hexane containing 5% AcOH)

Sources & evidence

ORD record
ord-3521eee6c9464833ae4f2e137a88410b
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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